Date nights for established couples can feel boring and stale if you talk about the same old topics all the time. Talking about work, the kids, or household repairs should not be the primary focus of nights when you’re trying to reconnect as a couple.

So, here is a list of 100 — yes, 100 — questions that you can choose from to ask each other on your next dinner out.

Use only two to three questions per date night, and really talk about the answers in depth. They range across various domains, including romance, intimacy, family, career, and many others.

The point is to get to know your partner on a deep level all over again. This will increase your feelings of closeness, connection, and romance, which we all know is the whole point of date night!


1. Questions to ask a guy You Like

1.          What is your favorite memory of dating me?

2.          What is your favorite sexual memory of us?

3.          What food reminds you of me?

4.          When was the last time you thought about me in a positive way?

5.          What is your favorite thing that I do for you?

6.          What movie reminds you of us?

7.          Which of your parents are you most like?

8.          Which of our kids are most like you? (or if you aren’t parents yet: Do you ever picture having kids?)

9.          What’s my best physical feature?

10.       What do you like most that I do in bed?

11.       What’s your favorite time of day to be intimate?

12.       Do you like kissing or hugging more?

13.       When did you know you wanted to be monogamous with me?

14.       Do you ever get jealous if you see me talking to other attractive people?

15.       Do you ever dream about me?

16.       What do you think we need to work on the most in our relationship?

17.       If you got sick, do you think I would be there to care for you?

18.       Do you believe that I love you?

19.       When did you know you wanted to kiss me?

20.       What’s your favorite non-sex activity that we do together?

2. 20 More Interesting Questions


1.           As a child, did you trust both of your parents?

2.          What is your favorite thing I ever did for a special occasion for you?

3.          What is your favorite sexual fantasy?

4.          What is your favorite sexual position?

5.          Do you ever think about me sexually during the day?

6.          What is something I could do to make you trust me even more?

7.          When do you feel the most protected and taken care of?

8.          What can I do to make sure you feel safe with me?

9.          When we hang out with friends, do I make you feel like you’re still my priority?

10.       When we are with my family, do I make you feel like you’re still my priority?

11.        Do you have any deal-breakers, things that would make you seriously reconsider our relationship?

12.       What was the very first thing you thought about me?

13.       When did you first think I was attractive?

14.       How long do you think people should wait before having kids?

15.       What did you learn about marriage from your parents?

16.       What did you learn about physical affection from your parents?

17.        What is your favorite book?

18.       What is your favorite song?

19.       What was your first favorite movie, as a child?

20.      What do you want to do when you retire?

3. Again 20 More Interesting Questions

1.           Do you ever picture having grandchildren?

2.          What’s another career that you think you would love?

3.          What’s your favorite physical feature of your own?

4.          Who was your favorite teacher when you were a child?

5.          What’s your favorite memory with your mom?

6.          What’s your favorite memory with your dad?

7.          Which significant other before me had the biggest impact on you?

8.          What did you think after your first sexual experience?

9.          Did you like high school or college better?

10.       Where have you always wanted to travel?

11.        Did you ever consider a totally different career path?

12.       What was your favorite class in high school?

13.       What was the best party you ever went to?

14.       What’s the happiest you ever felt?

15.       What’s the most anxious you ever felt?

16.       What’s the angriest you ever felt?

17.        Do you believe in God?

18.       What’s a question you’ve never asked me?

19.       What’s your favorite personality trait of your own?

20.      Which of your personality traits do you wish you could change?